Annie Billings was born around 1867 or 1868, likely in Vermont, though her birthplace was also listed as New York in some records. She first appeared in the 1870 U.S. Census as a 2-year-old living in Dorset, Vermont, with her parents, Justus and Sarah J. Billings, and siblings. By 1880, the family had moved to Altona, Clinton County, New York, and Annie was recorded as 12 years old and identified as mulatto.
In 1892, Annie was living in Greenwich, Washington County, New York, with Daniel and George Chapman. Her surname was listed as Chapman, suggesting she may have married one of the two men, though no marriage record was found. By 1894, she had returned to Vermont and was living in Rutland, working as a dressmaker and listed in the city directory as Mrs. Anna Chapman.
In January 1895, a newspaper noted that she was visiting her brother, B.L. Billings. By the 1900 Census, Anna was 32, single, and living with her parents again in Mendon, Vermont. She was raising a 10-year-old boy, Walter F. Chapman, believed to be her son, though no father was identified. Her race was recorded as white.
Anna Billings died of tuberculosis on May 16, 1902, at the age of 32 years, 5 months, and 27 days. Her death certificate confirmed her marital status as married, race as white, and birthplace as Mendon, Vermont. Her life was marked by shifts in location, race classification, and family structure, with limited documentation of her brief marriage and motherhood.